Showing Compound Card for beta-Bisabolene (CDB000088)

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Record Information
Version1.0
Created at2020-03-18 23:24:19 UTC
Updated at2020-12-07 19:07:05 UTC
CannabisDB IDCDB000088
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namebeta-Bisabolene
Descriptionbeta-Bisabolene is biochemically a sesquiterpenoid, comprised of three isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms. beta-Bisabolene is an isoprenoid lipid molecule which is very hydrophobic, practically insoluble in water, and relatively neutral. Bisabolene has three isomers (α-, β-, and γ-bisabolene) which differ by the positions of the double bonds. beta-Bisabolene has a balsamic odor. Bisabolenes are naturally occurring sesquiterpenoid found in the essential oils of bisabol from the shrub Commiphora guidottii, and in a wide variety of other plants including cubeb, lemon, oregano and in trace amounts in cannabis plants (PMID: 6991645 ). beta-Bisabolene is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Bisabolenes are also produced by different insects such as stink bugs, fruit flies (PMID:11673844 ) and by several fungi (PMID: 25957494 ). Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds, including hernandulcin, a natural sweetener (PMID: 22867794 ) which is approved as a food additive in Europe. beta-Bisabolene has some medicinal properties. It had synergistic antibacterial activity with ampicillin against Staphylococcus aureus (PMID: 17235483 ) and was cytotoxic to breast cancer cell lines (PMID: 26666387 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-beta-BisaboleneChEBI
(S)-(-)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadieneChEBI
(S)-1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexeneChEBI
L-beta-BisaboleneChEBI
(-)-b-BisaboleneGenerator
(-)-Β-bisaboleneGenerator
L-b-BisaboleneGenerator
L-Β-bisaboleneGenerator
b-BisaboleneGenerator
Β-bisaboleneGenerator
beta-BisaboleneChEBI
(S)-b-BisaboleneGenerator
(S)-Β-bisaboleneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(4S)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene
Traditional Name(-)-β-bisabolene
CAS Registry Number495-61-4
SMILES
CC(C)=CCCC(=C)[C@H]1CCC(C)=CC1
InChI Identifier
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1
InChI KeyXZRVRYFILCSYSP-OAHLLOKOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.01ALOGPS
logP4.88ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.28 m³·mol⁻¹ChemAxon
Polarizability26.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Tangerine DreamDetected and Quantified0.18 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8279897
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10104370
PDB IDNot Available
ChEBI ID49263
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Lu F, Teal PE: Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew). Arch Insect Biochem Physiol. 2001 Nov;48(3):144-54. doi: 10.1002/arch.1067. [PubMed:11673844 ]
  3. Spakowicz DJ, Strobel SA: Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential. Appl Microbiol Biotechnol. 2015 Jun;99(12):4943-51. doi: 10.1007/s00253-015-6641-y. Epub 2015 May 10. [PubMed:25957494 ]
  4. Attia M, Kim SU, Ro DK: Molecular cloning and characterization of (+)-epi-alpha-bisabolol synthase, catalyzing the first step in the biosynthesis of the natural sweetener, hernandulcin, in Lippia dulcis. Arch Biochem Biophys. 2012 Nov 1;527(1):37-44. doi: 10.1016/j.abb.2012.07.010. Epub 2012 Jul 31. [PubMed:22867794 ]
  5. Nascimento AM, Brandao MG, Oliveira GB, Fortes IC, Chartone-Souza E: Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus. Antonie Van Leeuwenhoek. 2007 Jul;92(1):95-100. doi: 10.1007/s10482-006-9139-x. Epub 2007 Jan 18. [PubMed:17235483 ]
  6. Yeo SK, Ali AY, Hayward OA, Turnham D, Jackson T, Bowen ID, Clarkson R: beta-Bisabolene, a Sesquiterpene from the Essential Oil Extract of Opoponax (Commiphora guidottii), Exhibits Cytotoxicity in Breast Cancer Cell Lines. Phytother Res. 2016 Mar;30(3):418-25. doi: 10.1002/ptr.5543. Epub 2015 Dec 15. [PubMed:26666387 ]